Montemassi Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Montemassi vacation rentals

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

1. Country House il Ciliegio

Roccastrada

Maaike

AED 356 total

includes taxes & fees

13 Nov - 14 Nov

A window with a view of a green landscape and a clear sky.

2. Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills

Roccastrada

AED 357 total

includes taxes & fees

10 Nov - 11 Nov

3. Villa Pianosa, Botri dei Lumachi

Toscana

AED 1,151 total

includes taxes & fees

7 Nov - 8 Nov

A rectangular infinity pool with clear water, surrounded by a stone deck, set against a backdrop of trees and a sunset.

4. Villa Giglio, Botri dei Lumachi

Toscana

AED 1,151 total

includes taxes & fees

7 Nov - 8 Nov

A person relaxing in a hot tub with a glass of wine.

5. Botrona B&B

Scarlino

Anna

AED 324 total

includes taxes & fees

11 Nov - 12 Nov

An outdoor dining area with stone walls, tables, and chairs.

6. Giacinto – Classic Double Room

Piloni

AED 464 total

includes taxes & fees

9 Nov - 10 Nov

A tree with a swing chair, a clear sky, and a distant tree.

7. Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi

Gavorrano

Anonymous traveler

AED 369 total

includes taxes & fees

24 Nov - 25 Nov

A patio with a round table and chairs, a window with blinds, and a view of trees and hills.

8. Panorama-Ferien-Toscana Your vacation home in Tuscany

Massa Marittima

stefano f.

AED 448 total

includes taxes & fees

19 Nov - 20 Nov

A building with arched windows and columns, potted plants on the balcony, and a stone wall.

9. Palazzo Malfatti - Two-room apartment for two people

Massa Marittima

AED 422 total

includes taxes & fees

30 Nov - 1 Dec

An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

10. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Braccagni

AED 465 total

includes taxes & fees

11 Nov - 12 Nov

A historic building with arched windows and a central emblem.

11. Palazzo Malfatti - Deluxe Apartment with a View of Piazza Garibaldi

Massa Marittima

Leslie T.

AED 633 total

includes taxes & fees

29 Nov - 30 Nov

12. Il Bennu - Breathtaking Views, a Panoramic Terrace, and Relaxation in Gavorrano

Gavorrano

AED 706 total

includes taxes & fees

24 Nov - 25 Nov

A stone building with a sign reading 'Ramos'.

13. Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning

Massa Marittima

AED 1,238 total

includes taxes & fees

7 Nov - 8 Nov

A stone building with outdoor seating and string lights.

14. Uva Spina – Intimate Double Room with Val di Farma View

Piloni

AED 520 total

includes taxes & fees

9 Nov - 10 Nov

A garden with a variety of plants, a palm tree, and a glass table with decorative items.

15. Il Bennu

Gavorrano

AED 700 total

includes taxes & fees

7 Nov - 8 Nov

16. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

Piloni

AED 631 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor dining area with stone walls and tables, surrounded by potted plants and string lights.

17. Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

Piloni

AED 687 total

includes taxes & fees

9 Nov - 10 Nov

A corridor with a vaulted ceiling, wooden doors, and artwork on the walls.

18. Palazzo Malfatti - Family Apartment for 4 People

Massa Marittima

AED 568 total

includes taxes & fees

7 Dec - 8 Dec

A courtyard with a stone staircase, potted plants, and a large rock sculpture.

19. Palazzo Malfatti - Two-Bedroom Apartment for 4 People

Massa Marittima

Nicola A.

AED 754 total

includes taxes & fees

30 Nov - 1 Dec

A kitchen with a wooden ceiling, a central island with bar stools, a fireplace, and a bookshelf.

20. Holiday Apartment 'Glicine' with Mountain View, Shared Pool & Wi-Fi

Montieri

AED 887 total

includes taxes & fees

19 Nov - 20 Nov

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Find vacation rentals that suit your style

Top Montemassi Hotel Reviews

A restaurant with outdoor seating, a bar area, and a view of the landscape.

B&B da Nada Locanda Toscana

Roccastrada

10/10 Excellent

We stayed here for three nights and had an incredible experience. The room was clean, offered a beautiful view, and had reliable Wi-Fi. The location is perfect for exploring, only an hour's drive to Montalcino and incredibly close to several fantastic wineries. The restaurant itself is absolutely fantastic: The panoramic views are amazing, the food is to die for (home cooking style), and the wine selection is excellent. Laura, her husband, and their son, Leonardo, are wonderful, welcoming...

Alexandre

A rustic interior with a stone fireplace, wooden bookshelves, and a traditional wooden staircase.

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Excellent

The Casa Del Chiodo was the perfect Tuscan B&B experience for us. From the moment Marco greeted us to the amazing multiple course evening meal that owner/chef Paola prepared to the breakfast served by Irene, it was the epitome of Italian hospitality. While the evening meal was extra, it was definitely worth it as it showcased local farm grown and hunted/gathered foods (such as mushrooms, venison and roasted chestnuts). Our room was clean, true to historical construction with modern amenities....

Nita Marie

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Excellent

Josh

An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

Agriturismo Giù al Pozzo

Gavorrano

10/10 Excellent

Micaiah

A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Excellent

Paul

A swimming pool with a waterfall feature, large windows, and a lounge chair.

Montebelli Agriturismo & Country Hotel

Gavorrano

10/10 Excellent

G&J

A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

Antico Casale L'Impostino

Civitella Paganico

10/10 Excellent

Mason

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

A cozy, open-plan restaurant with a wooden interior and a thatched roof.

Agriturismo Sweet Cottage

Grosseto

10/10 Excellent

The accommodations were very nice and the setting was very peaceful. Although our room had an unusual layout, it had everything we needed. Bedding was excellent. Air conditioning worked perfectly. Breakfast and dinners were wonderful. And the staff were SO friendly and helpful! This is convenient to the marina, Castiglione della Pescaia and central Grosseto. Is a great place to relax by the pool all day, go horseback riding or nearby shopping. We will be back!

John

A large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

10/10 Excellent

Matthew

A villa with a swimming pool, surrounded by trees and hills.

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

KEDARNATH

A pool with a modern water feature and a stone structure.

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

10/10 Excellent

Anonymous traveler

A stone wall with a view of rolling hills and mountains.

Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

10/10 Excellent

Castello Banfi - Il Borgo is either a great place to anchor your restoration or to invigorate your exploration. There's plenty to do on property: a wine tour through the high-tech wine production facility; wine tasting overlooking the Tuscan landscape (you have a substantial selection to choose from); lounging by the pool overlooking the many acres of grape vines, olive and plum trees, and the hills beyond; a visit to their glass museum; an intimate cooking class with one of the top Chefs in...

Greg

Frequently Asked Questions

Are there vacation rentals in Montemassi?

Yes, we give you a choice of vacation rentals near popular local attractions in Montemassi, or you can select a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Montemassi?

Casa Viale Italia - homely house with direct access to the sandy beach: Visitors like this Montemassi vacation home rental. It is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Montemassi?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Montemassi stay.

What’s there to see and do in Montemassi?

While exploring the area, visit family-friendly sights like Piscina Il Giunco, or get outside and enjoy nature at Lago dell'Accesa. Podere Ristella Vineyards and Winery and Rocca di Frassinello Winery are a couple of places you'll find in the larger area.

What’s a vacation rental in Montemassi like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Montemassi. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.

Montemassi Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montemassi vacation rentals

1. Country House il Ciliegio

2. Casa Giovy - Relaxation with a view stretching all the way to the sea, in the Tuscan hills

3. Villa Pianosa, Botri dei Lumachi

4. Villa Giglio, Botri dei Lumachi

5. Botrona B&B

6. Giacinto – Classic Double Room

7. Room 'Ghianda' with Shared Garden, Balcony and Wi-Fi

8. Panorama-Ferien-Toscana Your vacation home in Tuscany

9. Palazzo Malfatti - Two-room apartment for two people

10. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

11. Palazzo Malfatti - Deluxe Apartment with a View of Piazza Garibaldi

12. Il Bennu - Breathtaking Views, a Panoramic Terrace, and Relaxation in Gavorrano

13. Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning

14. Uva Spina – Intimate Double Room with Val di Farma View

15. Il Bennu

16. Deluxe Room 'Narciso Dei Poeti' with Extra Bed

17. Mora Selvatica – Deluxe Room with Private Balcony and Val di Farma View

18. Palazzo Malfatti - Family Apartment for 4 People

19. Palazzo Malfatti - Two-Bedroom Apartment for 4 People

20. Holiday Apartment 'Glicine' with Mountain View, Shared Pool & Wi-Fi

Find vacation rentals that suit your style

Top Montemassi Hotel Reviews

B&B da Nada Locanda Toscana

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Montemassi?

What's the top vacation rental in Montemassi?

How many vacation rentals are there in Montemassi?

What’s there to see and do in Montemassi?

What’s a vacation rental in Montemassi like?